I don’t think you’re doing anything “wrong” exactly, it’s just one of those things most pool owners wrestle with at some point. The challenge with solid winter covers is that once water and snow start to collect, gravity is always working against you. Air pillows help, but like you’ve seen, they can shift or lose air and then you’re back to square one.
One thing that helped me was tightening up the cover more than I thought I needed at the start. If the cover has too much slack, it naturally dips toward the center and makes a perfect bowl for water. I also started using a small automatic cover pump instead of waiting until the puddle got big, removing water as it accumulates keeps the weight from pulling the cover down further.
If you’re not ready to switch to a mesh safety cover like Zephyr mentioned, another trick is laying a couple of pool noodles or even a DIY frame under the cover alongside the air pillow. That way, even if the pillow shifts, you still have something breaking up the surface and encouraging water to move toward the edges. It’s a little bit of trial and error, but once you find the right setup for your pool size, it makes winter maintenance way less of a hassle.